Sailor Core Has Arrived — Get on Board
Sailing is the kind of thing that seems to be perpetually informing the way men dress, albeit discreetly. Perhaps it’s because the activity is aspirational — who wouldn’t want to own a sailboat and have the time to take said vessel out regularly? Or maybe it’s the wind-whipped, sun-kissed and salt-curled aesthetic that we strive for; a laissez-faire look earned at sea that exudes an effortless cool and a calm confidence.
Historically, the cues we’ve taken from our sea-faring brethren have run the gamut from overt to subtle, but by and large, they’ve been omnipresent in how we dress. When Paul Sperry introduced his iconic boat shoes and canvas deck sneakers, it was with sailing in mind. Sperry couldn’t have expected his shoes to become a staple of the coastal prep look that eventually swept across the United States, the U.K. and even Japan. What were once sailing shoes became foundational elements of the discerning mid-century man’s wardrobe — which we still look to for inspiration today. Also on the more overt end of the spectrum, you’ll find our infatuation with nautical stripes and the way they’ve become a menswear staple of sorts. Who doesn’t love a crisp white longsleeve with navy lines running across it?
Then there are the more subtle ways in which sailing and sea-faring have influenced the way we dress. Think of those iconic pictures of John F. Kennedy: the polo, the white pants, the Shetland wool sweater. Much of the making of JFK as an icon of style happened on a boat. And he’s not alone… so often, when we think of style icons, images of them sailing — or, at the very least, near the sea — come to mind, from Steve McQueen to Paul Newman and even the most stylish fictional characters like James Bond and Dickie Greenleaf.
Even the upper echelons of the luxury industry have been touched by sailing. One of Prada’s most instantly-recognizable sneakers is a sailing shoe named for the America’s Cup (more on that in a second), the iconic sailing competition that the Luna Rossa Prada Pirelli team competes for. The same can be said of Rolex, for whom one of the most iconic timepieces is the Yachtmaster, which, the tagline states, is “Made for Sailing.”
But if sailing’s influence is ubiquitous, why would one say it’s set to be a dominant trend in the coming months? For one, the boat shoe has enjoyed a much-publicized renaissance over the last year, reemerging as something people want to wear outside the confines of yacht clubs. In a way, it’s part of the revival of mid-to-late 2000s style and the prepwear codes that were heavily referenced in those years.
Then there’s Louis Vuitton, the luxury titan who always seems to be tapped into the zeitgeist, who wrested the America’s Cup sponsorship from fellow luxury behemoth Prada, starting with the 37th edition, being held in Barcelona this fall. If those two are competing to be the name associated with sailing’s premier event, there’s probably a reason. When the Louis Vuitton Cup (which allows teams to earn the right to challenge for the Louis Vuitton America’s Cup) starts, sailing is likely to become part of the cultural conversation. We’d be remiss to not cite Prada’s Fall-Winter 2024 collection, which featured a healthy dose of nautical cues.
So while it might be perpetually influential, sailing’s about to be a lot more noticeable in the coming months. Bearing that in mind, here’s what you need to look like you know how to skipper a boat.
Prada Linea Rossa Piqué Polo Shirt
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Prada’s technical Linea Rossa line, which translates to “red line” has become synonymous with modern, high performance sailing, thanks to the brand’s sponsorship of the Luna Rossa Prada Pirelli team. This lightweight shirt is waterproof, windproof and breathable, a testament to the brand’s technical innovation and a piece that’s easy to work into your wardrobe, whether you’re actually setting sail or just heading out in a thunderstorm. ($1,490)
Paul & Shark Velvet Cargo Trousers
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Paul & Shark’s DNA is infused with a nautical edge and these trousers tap into that, bringing together ruggedness and luxury to create a pant that will look as good as it feels. The straight leg and utilitarian detailing — deep pockets and flap fasteners — augment the nautical feel, but, if we’re being honest, it’s the fact these are white corduroy trousers that really taps into JFK’s and countless others — captain’s look. ($480)
Louis Vuitton x Timberland Ranger Boat Shoes
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Louis Vuitton is, at its heart, a travel brand. In 2024, we tend to associate planes with worldwide travel; however, when the Maison was founded (and during much of its early history), said travel would have taken place on sailboats and steamers. The Ranger Boat Shoe might not have the slick, streamlined silhouette of contemporary boat shoes — the ones meant to be worn when competing for the America’s Cup, say — but the ruggedness offers a streetwise touch that lends itself to being worn in the fall. These made-in-Italy nubuck boat shoes are best paired with a pair of wide-leg trousers, not unlike those mentioned above. ($1,470)
Prada America’s Cup Sneakers
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It would be impossible to talk about sailing’s influence on fashion — and the pieces to add to one’s wardrobe — without mentioning Prada’s now-iconic America’s Cup sneakers. Initially introduced in 1997 for the Luna Rossa crew, the America’s Cup became a popular silhouette even outside the sailing world, adopted, for example, by soccer fans in the UK. With its sporty shape, mixed materials and the recognizable sheen of the patent leather, the America’s Cup feels as at-home on deck as it does on the street. ($1,170)
BOSS Quilted Cotton-Silk Polo
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Every sailor needs a polo and this quilted cotton and silk one courtesy of BOSS more than does the trick. A crisp white polo always looks good, but the luxurious fabric and hand-feel makes this one even nicer, sufficiently elevated to be worn with a jacket for dinner at the yacht club after a day on the water. ($458)
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